Water → 5-Ethenyl-4-fluoro-2-nitrophenyl methyl ether

HRID 419449ノート

反応式

HRID 419449 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[C:7](Br)[C:6]([F:10])=[CH:5][C:4]=1[N+:11]([O-:13])=[O:12].O.[CH2:15](O)[CH2:16]C>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:15]=[CH2:16])[C:6]([F:10])=[CH:5][C:4]=1[N+:11]([O-:13])=[O:12]

参加物

5

反応物 3

HCID 962WaterHCID 10311-PropanolHCID 223473121-Bromo-2-fluoro-5-methoxy-4-nitrobenzene

生成物 1

HCID 594529635-Ethenyl-4-fluoro-2-nitrophenyl methyl ether収率 86%

試薬・触媒・溶媒 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒

反応条件

温度
100 °C

実験手順

To 5-bromo-4-fluoro-2-nitrophenyl methyl ether (4.0 g, 16 mmol) in 40 mL of n-propanol was added, PdCl2(dppf)*DCM (0.234 g, 0.31 mmol), potassium ethenyl(trifluoro)borate (2.57 g, 19.2 mmol), and TEA (1.62 g, 16 mmol). The mixture was heated to 100° C. for 3 h. The mixture was poured into 250 mL of H2O and extracted with DCM, dried (Na2SO4), filtered, and rotovaped down to give the title compound of step B (2.73 g, 13.84 mmol, 86%). 1H NMR (400 MHz, CDCl3) δ ppm 7.64 (d, J=9.52 Hz, 1H), 7.11 (d, J=6.04 Hz, 1H), 6.84 (dd, J=17.76, 11.17 Hz, 1H), 5.95 (d, J=17.76 Hz, 1H), 5.59 (d, J=11.17 Hz, 1H), 3.97 (s, 3H).

後処理

  1. extractionextracted with DCM
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered

出典と根拠

ORDレコード
ord-3897d6db7ccb49e480673702b0aaa5fa
出典データセット
uspto-grants-2012_01
特許番号
US08093239B2

反応ノート

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